Hi Laura,

Thanks for your help.  I've captured one of the SMTP transactions:


SMTP<< 220 mx.google.com ESMTP ffacd0b85a97d-37308269cdfsi4917634f8f.703 - gsmtp
 SMTP>> EHLO mailhost.maildomain.net
 SMTP<< 250-mx.google.com at your service, [555.555.555.555]
        250-SIZE 157286400
        250-8BITMIME
        250-STARTTLS
        250-ENHANCEDSTATUSCODES
        250-PIPELINING
        250-CHUNKING
        250 SMTPUTF8
 SMTP>> STARTTLS
 SMTP<< 220 2.0.0 Ready to start TLS
 SMTP>> EHLO mailhost.maildomain.net
 SMTP<< 250-mx.google.com at your service, [555.555.555.555]
        250-SIZE 157286400
        250-8BITMIME
        250-ENHANCEDSTATUSCODES
        250-PIPELINING
        250-CHUNKING
        250 SMTPUTF8
 SMTP>> MAIL FROM:<> SIZE=1862
 SMTP>> RCPT TO:<gmailu...@gmail.com>
        will write message using CHUNKING
 SMTP>> BDAT 646 LAST
 SMTP<< 250 2.1.0 OK ffacd0b85a97d-37308269cdfsi4917634f8f.703 - gsmtp
 SMTP<< 250 2.1.5 OK ffacd0b85a97d-37308269cdfsi4917634f8f.703 - gsmtp
 SMTP<< 550-5.7.26 Your email has been blocked because the sender is unauthenticated.         550-5.7.26 Gmail requires all senders to authenticate with either SPF or DKIM.
        550-5.7.26
        550-5.7.26  Authentication results:
        550-5.7.26  DKIM = did not pass
        550-5.7.26  SPF [] with ip: [555.555.555.555] = did not pass
        550-5.7.26
        550-5.7.26  For instructions on setting up authentication, go to
        550 5.7.26 https://support.google.com/mail/answer/81126#authentication ffacd0b85a97d-37308269cdfsi4917634f8f.703 - gsmtp
 SMTP>> QUIT
 SMTP(close)>>


I''ve double checked that the EHLO works with the SPF (in the redacted log, IP 555.555.555.555 matches maildomain.net's SPF):

That is why I find this so weird.   I know DKIM is not setup there, but the SPF is and it is being ignored or not checked properly.

Best regards


On 27/8/24 13:28, Laura Atkins wrote:
You need to authenticate with either SPF or DKIM. As you’re using a null sender, you can set up SPF on the EHLO value. Or you can sign outgoing mail with DKIM, dealer’s choice.

laura

On 27 Aug 2024, at 11:56, Eduardo Diaz Comellas via mailop <mailop@mailop.org> wrote:

Hi all,

I've got a couple of complains from customers saying that the vacation message is not being received by Gmail users. Our email service is quite standard, with dovecot+sieve processing the email storage and autoresponders.

I've confirmed that the problem is true:

2024-08-27 11:08:09 1sisBN-002eWx-KM <= <> H=(mydovecot.host) [172.30.6.182] P=esmtp K S=1087 id=dovecot-sieve-1724749689-16845...@mydovecot.host 2024-08-27 11:08:10 1sisBN-002eWx-KM ** randomgmailu...@gmail.com R=hubbed_hosts T=remote_smtp H=gmail-smtp-in.l.google.com [173.194.76.27] X=TLS1.3:ECDHE_X25519__ECDSA_SECP256R1_SHA256__AES_256_GCM:256 CV=yes DN="CN=mx.google.com": SMTP error from remote mail server after pipelined end of data: 550-5.7.26 Your email has been blocked because the sender is unauthenticated.\n550-5.7.26 Gmail requires all senders to authenticate with either SPF or DKIM.\n550-5.7.26\n550-5.7.26  Authentication results:\n550-5.7.26  DKIM = did not pass\n550-5.7.26 SPF [] with ip: [555.555.555.555] = did not pass\n550-5.7.26\n550-5.7.26  For instructions on setting up authentication, go to\n550 5.7.26 https://support.google.com/mail/answer/81126#authentication ffacd0b8rr97d-373081420c7si4806836f8f.262 - gsmtp
2024-08-27 11:08:10 1sisBN-002eWx-KM Frozen (delivery error message)


I think that sending the vacation messages with null sender is an standard practise and the best way to avoid loops. I've found no problems with any other email providers: only gmail is blocking this messages.

Does anyone have this issue? How do you deal with it?

Best regards.

--
Eduardo Díaz Comellas
Ultreia Comunicaciones, S.L.

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--
The Delivery Expert

Laura Atkins
Word to the Wise
la...@wordtothewise.com

Delivery hints and commentary: http://wordtothewise.com/blog






--
Eduardo Díaz Comellas
Ultreia Comunicaciones, S.L.
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